5-Bromo-2-(4-fluoro­phen­yl)-3-phenyl­sulfinyl-1-benzofuran

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811032387

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2346

doi:10.1107/S1600536811032387

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5-Bromo-2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 8 August 2011; accepted 10 August 2011; online 17 August 2011)

In the title compound, C₂₀H₁₂BrFO₂S, the 4-fluorophenyl ring makes a dihedral angle of 2.63 (6)° with the mean plane of the benzofuran fragment. The dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds, and slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.719 (3) Å, interplanar distance = 3.000 (3) Å and slippage = 1.520 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 5-halo-2-(4-halophenyl)-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2010 , 2011 ).

Experimental

Crystal data

C₂₀H₁₂BrFO₂S
M_r = 415.27
Triclinic, $[P \overline 1]$
a = 8.0090 (2) Å
b = 9.8607 (3) Å
c = 11.7209 (3) Å
α = 70.471 (2)°
β = 83.171 (2)°
γ = 69.583 (2)°
V = 817.59 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.66 mm⁻¹
T = 173 K
0.29 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.513, T_max = 0.649
15330 measured reflections
4102 independent reflections
3428 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.082
S = 1.02
4102 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.58	3.460 (2)	154
C19—H19⋯O2ⁱⁱ	0.95	2.55	3.413 (3)	150
Symmetry codes: (i) x-1, y+1, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032387/zl2399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032387/zl2399Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032387/zl2399Isup3.cml

checkCIF report

Comment top

Many compounds containing a benzofuran ring system have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 5-halo-2-(4-halophenyl)-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 2.63 (6)°, and the dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a 4-fluorophenyl H atom and the O atom of the sulfinyl group (Table 1; C13—H13···O2ⁱ), and the second one between a phenyl H atom and the O atom of the sulfinyl group (Table 1; C19—H19···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by weak slipped π–π interactions between the benzene rings of adjacent molecules, with Cg···Cgⁱⁱⁱ distance of 3.719 (3) Å and an interplanar distance of 3.000 (3) Å resulting in a slippage of 1.520 (3) Å (Cg is the centroids of the C2–C7 benzene ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 5-halo-2-(4-halophenyl)-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-2-(4-fluorophenyl)-3-phenylsulfanyl-1-benzofuran (319 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 67%, m.p. 473–474 K; Rf = 0.70 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and π–π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1, y + 1, z; (ii) x - 1, y, z; (iii) - x + 1, - y + 1, - z; (iv) x + 1, y - 1, z; (v) x + 1, y, z.]

5-Bromo-2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₀H₁₂BrFO₂S	Z = 2
M_r = 415.27	F(000) = 416
Triclinic, P1	D_x = 1.687 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0090 (2) Å	Cell parameters from 5582 reflections
b = 9.8607 (3) Å	θ = 2.3–28.3°
c = 11.7209 (3) Å	µ = 2.66 mm⁻¹
α = 70.471 (2)°	T = 173 K
β = 83.171 (2)°	Block, colourless
γ = 69.583 (2)°	0.29 × 0.19 × 0.18 mm
V = 817.59 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	4102 independent reflections
Radiation source: rotating anode	3428 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.039
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.5°, θ_min = 1.8°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.513, T_max = 0.649	l = −15→15
15330 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: difference Fourier map
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0418P)² + 0.2246P] where P = (F_o² + 2F_c²)/3
4102 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₁₂BrFO₂S	γ = 69.583 (2)°
M_r = 415.27	V = 817.59 (4) Å³
Triclinic, P1	Z = 2
a = 8.0090 (2) Å	Mo Kα radiation
b = 9.8607 (3) Å	µ = 2.66 mm⁻¹
c = 11.7209 (3) Å	T = 173 K
α = 70.471 (2)°	0.29 × 0.19 × 0.18 mm
β = 83.171 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4102 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3428 reflections with I > 2σ(I)
T_min = 0.513, T_max = 0.649	R_int = 0.039
15330 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
4102 reflections	Δρ_min = −0.35 e Å⁻³
226 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	1.00885 (3)	0.24519 (3)	−0.107040 (19)	0.03957 (9)
S1	0.63342 (6)	0.12842 (5)	0.38339 (4)	0.02592 (11)
F1	0.02314 (18)	0.62109 (15)	0.66048 (12)	0.0443 (3)
O2	0.8243 (2)	0.04378 (17)	0.36866 (14)	0.0362 (3)
O1	0.49496 (18)	0.57208 (14)	0.20182 (11)	0.0254 (3)
C2	0.6785 (2)	0.3543 (2)	0.16790 (16)	0.0229 (4)
C1	0.5920 (2)	0.3166 (2)	0.28359 (16)	0.0228 (4)
C3	0.7985 (3)	0.2720 (2)	0.09969 (17)	0.0256 (4)
H3	0.8443	0.1637	0.1280	0.031*
C4	0.8479 (3)	0.3543 (2)	−0.01080 (18)	0.0279 (4)
C5	0.7855 (3)	0.5135 (2)	−0.05501 (18)	0.0301 (4)
H5	0.8259	0.5651	−0.1311	0.036*
C6	0.6651 (3)	0.5955 (2)	0.01210 (18)	0.0287 (4)
H6	0.6194	0.7038	−0.0163	0.034*
C7	0.6142 (3)	0.5126 (2)	0.12269 (17)	0.0242 (4)
C8	0.4834 (3)	0.4504 (2)	0.30045 (16)	0.0228 (4)
C9	0.3606 (3)	0.4920 (2)	0.39482 (17)	0.0237 (4)
C10	0.3378 (3)	0.3843 (2)	0.50252 (19)	0.0312 (4)
H10	0.4015	0.2792	0.5148	0.037*
C11	0.2245 (3)	0.4274 (2)	0.59151 (19)	0.0332 (5)
H11	0.2097	0.3534	0.6649	0.040*
C12	0.1332 (3)	0.5797 (2)	0.57210 (19)	0.0301 (4)
C13	0.1499 (3)	0.6903 (2)	0.4678 (2)	0.0347 (5)
H13	0.0843	0.7948	0.4563	0.042*
C14	0.2647 (3)	0.6456 (2)	0.37981 (19)	0.0314 (4)
H14	0.2791	0.7209	0.3072	0.038*
C15	0.5071 (3)	0.0727 (2)	0.30151 (17)	0.0259 (4)
C16	0.5951 (3)	−0.0160 (2)	0.2292 (2)	0.0336 (5)
H16	0.7214	−0.0485	0.2233	0.040*
C17	0.4956 (4)	−0.0567 (3)	0.1652 (2)	0.0446 (6)
H17	0.5534	−0.1162	0.1138	0.054*
C18	0.3125 (4)	−0.0105 (3)	0.1765 (2)	0.0474 (6)
H18	0.2446	−0.0366	0.1311	0.057*
C19	0.2264 (3)	0.0733 (3)	0.2530 (2)	0.0450 (6)
H19	0.1006	0.1015	0.2622	0.054*
C20	0.3238 (3)	0.1155 (2)	0.3157 (2)	0.0334 (5)
H20	0.2660	0.1734	0.3682	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03834 (14)	0.04542 (15)	0.03048 (13)	−0.01050 (10)	0.01344 (9)	−0.01439 (10)
S1	0.0273 (2)	0.0205 (2)	0.0210 (2)	−0.00211 (18)	0.00143 (19)	−0.00188 (17)
F1	0.0399 (7)	0.0455 (7)	0.0390 (7)	−0.0019 (6)	0.0137 (6)	−0.0202 (6)
O2	0.0258 (7)	0.0315 (7)	0.0387 (8)	0.0015 (6)	−0.0035 (6)	−0.0055 (6)
O1	0.0326 (7)	0.0201 (6)	0.0209 (6)	−0.0079 (5)	0.0021 (6)	−0.0048 (5)
C2	0.0243 (9)	0.0248 (9)	0.0187 (9)	−0.0092 (7)	0.0003 (7)	−0.0047 (7)
C1	0.0236 (9)	0.0226 (9)	0.0195 (9)	−0.0066 (7)	0.0007 (7)	−0.0047 (7)
C3	0.0242 (9)	0.0254 (9)	0.0241 (9)	−0.0065 (7)	0.0007 (8)	−0.0058 (7)
C4	0.0242 (9)	0.0345 (10)	0.0234 (9)	−0.0100 (8)	0.0038 (8)	−0.0080 (8)
C5	0.0331 (11)	0.0353 (11)	0.0220 (9)	−0.0171 (9)	0.0039 (8)	−0.0043 (8)
C6	0.0358 (11)	0.0259 (9)	0.0244 (10)	−0.0147 (8)	0.0007 (8)	−0.0035 (8)
C7	0.0268 (9)	0.0245 (9)	0.0214 (9)	−0.0097 (7)	−0.0001 (8)	−0.0061 (7)
C8	0.0280 (9)	0.0209 (8)	0.0190 (9)	−0.0091 (7)	−0.0012 (7)	−0.0040 (7)
C9	0.0235 (9)	0.0239 (9)	0.0226 (9)	−0.0059 (7)	−0.0022 (7)	−0.0073 (7)
C10	0.0352 (11)	0.0223 (9)	0.0309 (11)	−0.0052 (8)	0.0064 (9)	−0.0086 (8)
C11	0.0368 (11)	0.0292 (10)	0.0263 (10)	−0.0067 (9)	0.0069 (9)	−0.0063 (8)
C12	0.0240 (10)	0.0361 (11)	0.0297 (10)	−0.0047 (8)	0.0033 (8)	−0.0162 (9)
C13	0.0339 (11)	0.0261 (10)	0.0366 (12)	0.0006 (8)	0.0005 (9)	−0.0119 (9)
C14	0.0350 (11)	0.0233 (9)	0.0286 (10)	−0.0035 (8)	−0.0002 (9)	−0.0055 (8)
C15	0.0275 (10)	0.0174 (8)	0.0254 (10)	−0.0046 (7)	0.0025 (8)	−0.0013 (7)
C16	0.0375 (12)	0.0239 (9)	0.0374 (12)	−0.0103 (9)	0.0101 (9)	−0.0105 (9)
C17	0.0620 (17)	0.0308 (11)	0.0455 (14)	−0.0202 (11)	0.0068 (12)	−0.0150 (10)
C18	0.0621 (17)	0.0348 (12)	0.0478 (15)	−0.0278 (12)	−0.0128 (13)	0.0004 (11)
C19	0.0351 (12)	0.0371 (12)	0.0531 (15)	−0.0134 (10)	−0.0069 (11)	0.0017 (11)
C20	0.0294 (10)	0.0271 (10)	0.0347 (11)	−0.0054 (8)	0.0046 (9)	−0.0042 (9)

Geometric parameters (Å, º) top

Br1—C4	1.895 (2)	C9—C14	1.399 (3)
S1—O2	1.4852 (15)	C10—C11	1.377 (3)
S1—C1	1.7698 (18)	C10—H10	0.9500
S1—C15	1.794 (2)	C11—C12	1.373 (3)
F1—C12	1.353 (2)	C11—H11	0.9500
O1—C7	1.371 (2)	C12—C13	1.369 (3)
O1—C8	1.382 (2)	C13—C14	1.378 (3)
C2—C3	1.389 (3)	C13—H13	0.9500
C2—C7	1.391 (3)	C14—H14	0.9500
C2—C1	1.441 (3)	C15—C16	1.380 (3)
C1—C8	1.368 (3)	C15—C20	1.385 (3)
C3—C4	1.376 (3)	C16—C17	1.387 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.397 (3)	C17—C18	1.380 (4)
C5—C6	1.380 (3)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.383 (4)
C6—C7	1.383 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.375 (3)
C8—C9	1.457 (3)	C19—H19	0.9500
C9—C10	1.392 (3)	C20—H20	0.9500

O2—S1—C1	106.67 (9)	C11—C10—H10	119.5
O2—S1—C15	106.92 (9)	C9—C10—H10	119.5
C1—S1—C15	96.40 (9)	C12—C11—C10	118.66 (19)
C7—O1—C8	106.92 (14)	C12—C11—H11	120.7
C3—C2—C7	119.62 (17)	C10—C11—H11	120.7
C3—C2—C1	135.37 (17)	F1—C12—C13	119.07 (18)
C7—C2—C1	105.00 (16)	F1—C12—C11	118.23 (18)
C8—C1—C2	107.45 (16)	C13—C12—C11	122.70 (19)
C8—C1—S1	128.60 (15)	C12—C13—C14	118.04 (19)
C2—C1—S1	123.90 (14)	C12—C13—H13	121.0
C4—C3—C2	116.94 (18)	C14—C13—H13	121.0
C4—C3—H3	121.5	C13—C14—C9	121.58 (19)
C2—C3—H3	121.5	C13—C14—H14	119.2
C3—C4—C5	123.30 (19)	C9—C14—H14	119.2
C3—C4—Br1	117.97 (15)	C16—C15—C20	121.5 (2)
C5—C4—Br1	118.73 (15)	C16—C15—S1	119.32 (16)
C6—C5—C4	119.88 (18)	C20—C15—S1	119.10 (16)
C6—C5—H5	120.1	C15—C16—C17	118.7 (2)
C4—C5—H5	120.1	C15—C16—H16	120.6
C5—C6—C7	116.77 (18)	C17—C16—H16	120.6
C5—C6—H6	121.6	C18—C17—C16	119.8 (2)
C7—C6—H6	121.6	C18—C17—H17	120.1
O1—C7—C6	125.82 (17)	C16—C17—H17	120.1
O1—C7—C2	110.70 (16)	C17—C18—C19	120.9 (2)
C6—C7—C2	123.48 (18)	C17—C18—H18	119.6
C1—C8—O1	109.92 (16)	C19—C18—H18	119.6
C1—C8—C9	135.27 (17)	C20—C19—C18	119.7 (2)
O1—C8—C9	114.80 (15)	C20—C19—H19	120.2
C10—C9—C14	117.93 (18)	C18—C19—H19	120.2
C10—C9—C8	122.43 (17)	C19—C20—C15	119.3 (2)
C14—C9—C8	119.61 (17)	C19—C20—H20	120.4
C11—C10—C9	121.09 (18)	C15—C20—H20	120.4

C3—C2—C1—C8	−178.7 (2)	C7—O1—C8—C9	−179.65 (16)
C7—C2—C1—C8	0.2 (2)	C1—C8—C9—C10	3.7 (4)
C3—C2—C1—S1	3.7 (3)	O1—C8—C9—C10	−177.40 (18)
C7—C2—C1—S1	−177.34 (14)	C1—C8—C9—C14	−178.2 (2)
O2—S1—C1—C8	−143.48 (18)	O1—C8—C9—C14	0.7 (3)
C15—S1—C1—C8	106.68 (19)	C14—C9—C10—C11	0.0 (3)
O2—S1—C1—C2	33.56 (19)	C8—C9—C10—C11	178.1 (2)
C15—S1—C1—C2	−76.27 (17)	C9—C10—C11—C12	0.1 (3)
C7—C2—C3—C4	0.3 (3)	C10—C11—C12—F1	−179.5 (2)
C1—C2—C3—C4	179.1 (2)	C10—C11—C12—C13	0.2 (3)
C2—C3—C4—C5	0.9 (3)	F1—C12—C13—C14	179.0 (2)
C2—C3—C4—Br1	−179.14 (14)	C11—C12—C13—C14	−0.6 (3)
C3—C4—C5—C6	−1.5 (3)	C12—C13—C14—C9	0.8 (3)
Br1—C4—C5—C6	178.56 (16)	C10—C9—C14—C13	−0.5 (3)
C4—C5—C6—C7	0.8 (3)	C8—C9—C14—C13	−178.7 (2)
C8—O1—C7—C6	−179.84 (19)	O2—S1—C15—C16	−8.11 (18)
C8—O1—C7—C2	0.7 (2)	C1—S1—C15—C16	101.52 (16)
C5—C6—C7—O1	−179.09 (19)	O2—S1—C15—C20	169.70 (15)
C5—C6—C7—C2	0.3 (3)	C1—S1—C15—C20	−80.67 (16)
C3—C2—C7—O1	178.60 (17)	C20—C15—C16—C17	3.0 (3)
C1—C2—C7—O1	−0.6 (2)	S1—C15—C16—C17	−179.24 (16)
C3—C2—C7—C6	−0.9 (3)	C15—C16—C17—C18	−1.1 (3)
C1—C2—C7—C6	179.93 (19)	C16—C17—C18—C19	−1.5 (3)
C2—C1—C8—O1	0.2 (2)	C17—C18—C19—C20	2.2 (3)
S1—C1—C8—O1	177.59 (14)	C18—C19—C20—C15	−0.3 (3)
C2—C1—C8—C9	179.1 (2)	C16—C15—C20—C19	−2.3 (3)
S1—C1—C8—C9	−3.5 (4)	S1—C15—C20—C19	179.90 (16)
C7—O1—C8—C1	−0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.58	3.460 (2)	154
C19—H19···O2ⁱⁱ	0.95	2.55	3.413 (3)	150

Symmetry codes: (i) x−1, y+1, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂BrFO₂S
M_r	415.27
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.0090 (2), 9.8607 (3), 11.7209 (3)
α, β, γ (°)	70.471 (2), 83.171 (2), 69.583 (2)
V (Å³)	817.59 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.66
Crystal size (mm)	0.29 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.513, 0.649
No. of measured, independent and observed [I > 2σ(I)] reflections	15330, 4102, 3428
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.082, 1.02
No. of reflections	4102
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.58	3.460 (2)	153.5
C19—H19···O2ⁱⁱ	0.95	2.55	3.413 (3)	150.3

Symmetry codes: (i) x−1, y+1, z; (ii) x−1, y, z.

References

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Volume 67| Part 9| September 2011| Page o2346

doi:10.1107/S1600536811032387

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